Saralasin

Saralasin

Names
IUPAC name (2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(methylamino)acetyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]propanoic acid
Other names Sar-Arg-Val-Tyr-Val-His-Pro-Ala
Identifiers
CAS Number	34273-10-4 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL938 N ChEMBL1200670 N
ChemSpider	4884380 N
PubChem CID	6324663
UNII	H2AFV2HE66 N
CompTox Dashboard (EPA)	DTXSID2046549
InChI InChI=1S/C42H65N13O10/c1-22(2)33(53-35(58)28(50-32(57)20-45-6)9-7-15-47-42(43)44)38(61)51-29(17-25-11-13-27(56)14-12-25)36(59)54-34(23(3)4)39(62)52-30(18-26-19-46-21-48-26)40(63)55-16-8-10-31(55)37(60)49-24(5)41(64)65/h11-14,19,21-24,28-31,33-34,45,56H,7-10,15-18,20H2,1-6H3,(H,46,48)(H,49,60)(H,50,57)(H,51,61)(H,52,62)(H,53,58)(H,54,59)(H,64,65)(H4,43,44,47)/t24-,28-,29-,30-,31-,33-,34-/m0/s1 N Key: PFGWGEPQIUAZME-NXSMLHPHSA-N N InChI=1/C42H65N13O10/c1-22(2)33(53-35(58)28(50-32(57)20-45-6)9-7-15-47-42(43)44)38(61)51-29(17-25-11-13-27(56)14-12-25)36(59)54-34(23(3)4)39(62)52-30(18-26-19-46-21-48-26)40(63)55-16-8-10-31(55)37(60)49-24(5)41(64)65/h11-14,19,21-24,28-31,33-34,45,56H,7-10,15-18,20H2,1-6H3,(H,46,48)(H,49,60)(H,50,57)(H,51,61)(H,52,62)(H,53,58)(H,54,59)(H,64,65)(H4,43,44,47)/t24-,28-,29-,30-,31-,33-,34-/m0/s1 Key: PFGWGEPQIUAZME-NXSMLHPHBA
SMILES C[C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC2=CN=CN2)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)CNC
Properties
Chemical formula	C42H65N13O10
Molar mass	912.05 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Saralasin is a competitive angiotensin II receptor antagonist with partial agonist activity. The aminopeptide sequence for saralasin differs from angiotensin II at three sites. At position 1, sarcosine replaces aspartic acid increasing the affinity for vascular smooth muscle receptors and making the peptide resistant to degradation by aminopeptidases Pals et al (1979). At position 5, isoleucine is replaced by valine, and at position 8, phenylalanine is replaced by alanine which leads to a smaller stimulatory effect. Saralasin was used to distinguish renovascular hypertension from essential hypertension prior to its discontinuation in January, 1984 because of a number of false-positive and false-negative reports Hutchison and Shahan (2004).

External links

• Saralasin at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
• Olsson M, Annerbrink K, Hedner J, Eriksson E (2004). "Intracerebroventricular administration of the angiotensin II receptor antagonist saralasin reduces respiratory rate and tidal volume variability in freely moving Wistar rats". Psychoneuroendocrinology. 29 (1): 107–12. doi:10.1016/S0306-4530(02)00147-6. PMID 14575733. S2CID 44451942.
• Ip S, Tsang S, Wong T, Che C, Leung P (2003). "Saralasin, a nonspecific angiotensin II receptor antagonist, attenuates oxidative stress and tissue injury in cerulein-induced acute pancreatitis". Pancreas. 26 (3): 224–9. doi:10.1097/00006676-200304000-00003. PMID 12657946. S2CID 28646144.
• Tsang S, Ip S, Wong T, Che C, Leung P (2003). "Differential effects of saralasin and ramiprilat, the inhibitors of renin-angiotensin system, on cerulein-induced acute pancreatitis". Regul Pept. 111 (1–3): 47–53. doi:10.1016/S0167-0115(02)00226-4. PMID 12609748. S2CID 2150707.